N-bromobutanimide → HCID 86137547, compound

HRID 579366Notes

Reaction equation

HRID 579366 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH3:13])[C:5](=[O:14])[CH:4]=1.[Br:15]N1C(=O)CCC1=O>C1COCC1>[Br:15][C:4]1[C:5](=[O:14])[N:6]([CH3:13])[C:7]2[C:12]([C:3]=1[O:2][CH3:1])=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1820732(1H)-Quinolinone, 4-methoxy-1-methyl-

Product 1

HCID 86137547HCID 86137547, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-methoxy-1-methylquinolin-2(1H)-one (2 g, 10.57 mmol) in THF (5 mL) at 0° C. under N2 atmosphere was added N-bromosuccinimide (2.26 g, 12.68 mmol) in portions over a period of 1 hour. The suspension was stirred at 0° C. for 1 hour then at room temperature for 2 hours. The solvent was removed in vacuo and CH2Cl2 was added to re-dissolve the residue. The solution was washed twice with a cold saturated NaHCO3 solution and with cold H2O then dried over anhydrous MgSO4. The solvent was removed in vacuo and the resulting solid residue was triturated several times with Et2O. The resulting solid was dried in vacuo to afford 3-bromo-4-methoxy-1-methylquinolin-2(1H)-one (2.7 g, MS: 269.9 [M+H+])

Workup

  1. waitat room temperature for 2 hours
  2. customThe solvent was removed in vacuo and CH2Cl2
  3. additionwas added
  4. dissolutionto re-dissolve the residue
  5. washThe solution was washed twice with a cold saturated NaHCO3 solution and with cold H2O
  6. dry with materialthen dried over anhydrous MgSO4
  7. customThe solvent was removed in vacuo
  8. customthe resulting solid residue was triturated several times with Et2O
  9. customThe resulting solid was dried in vacuo

Sources & evidence

ORD record
ord-d9c47bcef54f449a8b69f841952c5310
Source dataset
uspto-grants-2015_05
Patent number
US09040712B2

Reaction notes

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